# From $100M Exit to Fulfilment: Josh Payne’s Playbook

Page: https://stenobird.com/podcast/exit-paradox-7495448/from-100m-exit-to-fulfilment-josh-payne-s-playbook
Text version: https://stenobird.com/podcast/exit-paradox-7495448/from-100m-exit-to-fulfilment-josh-payne-s-playbook.md
Podcast: [Exit Paradox](https://stenobird.com/podcast/exit-paradox-7495448)
Published: 2025-02-28T19:05:54+00:00
Episode link: https://www.exitparadox.com/podcast/josh-payne
Audio file: https://media.transistor.fm/94f26f6e/5b9a62d4.mp3
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JSON: https://stenobird.com/v1/public/podcasts/exit-paradox-7495448/episodes/from-100m-exit-to-fulfilment-josh-payne-s-playbook
Duration seconds: 3317

## Resource

My guest today, Josh Payne, has developed fascinating insights and systems to do just that. Josh sold his company, Stack Commerce, for nearly $100 million 4 years ago. A huge milestone - but as all exited founders know, the real story starts after the deal is done.Today, he’s building again - but with a completely different approach. Josh isn’t optimizing for another massive exit. He’s after something bigger. So let’s see what we can learn from this fascinating man. 00:00:00 Introduction 00:00:45 Selling StackCommerce: Was It a Happy Moment? 00:02:00 The Emotional Impact of Selling a Company 00:03:30 Why Money Didn’t Solve Everything 00:05:15 Prioritizing Family After the Exit 00:06:30 Leaving the Company: A Tough Identity Shift 00:07:45 Taking a Healing Family Trip 00:09:00 Training for an Ironman & Overcoming Mental Barriers 00:12:30 Decoupling Identity from Business 00:14:00 Leadership & Purpose Beyond Business 00:16:00 Sacrifice vs. Suffering in Entrepreneurship 00:18:45 Ironman Training: Lessons in Overcoming Fear 00:22:00 The Challenge of Finding a New Purpose 00:23:45 Why Start Another Business After an Exit? 00:27:00 Learning to Build a Company Without Fear 00:30:00 The Difference Between First and Second Businesses 00:33:00 Finding a Sustainable Way to Build Again 00:35:00 Balancing Business & Personal Life After Exit 00:38:15 Why Many Second Businesses Fail 00:42:00 The Importance of Motivation in a New Startup 00:45:30 Avoiding the Trap of Losing Interest Midway 00:48:00 The Role of Peer Groups Like Tiger 21 00:50:30 How Long Does It Take to Truly Adjust After Exit? 00:53:00 Raising Kids With Wealth: Teaching Responsibility 00:54:00 Closing Thoughts & Future Plans

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